2-Methyl-3-buten-2-ol → HCID 14710051, compound

Participants

Reaction Steps

To a mixture of 2,6-dimethylphenol (122 g, 1 mol) and 85% phosphoric acid (60 mL) was added 2-methyl-3-buten-2-ol (103 g, 1.2 mol) with efficient stirring at 35°-43° C. during 1 h. After stirring for an additional 3.5 h at 25° C., the mixture was quenched into ice and extracted with hexane. The combined hexane extracts were washed successively with 1 N sodium hydroxide (100 mL), 5% sodium bicarbonate (300 mL) and brine (200 mL). The organic layer was dried, the solvent evaporated, and the residue fractionated to yield 92 g of 2,6-dimethyl-4-(3-methyl-2-butenyl)phenol bp 108°-111° C. (1 mm). NMR (CDCl3) δ1.7 (6H, s), 2.2 (6H, s), 3.2 (2H, bd), 4.4 (1H, s, exchanged with D2O), 5.3 (1H, m), 6.8 (2H, s). IR (film) 3500, 1225, 1150, 870 cm-1. MS (m/e) 190 (M+), 175, 160, 135, 91.

Provenance & Evidence